Enzymatic acyl exchange to vary saturation in di‐ and triglycerides

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Abstract
The reactionrac‐glyceryl‐1‐palmitate‐2,3‐dioleate(POO) and palmitic acid(P) (excess) → glyceryl‐2‐oleate‐1, 3‐dipalmitate(POP) + O catalyzed by porcine pancreatic lipase is a model for the general reactionAAA′’ +A′’ → A′'AA′’ +A.(P,O,A = palmitoyl, oleyl, acyl groups or palmitic, oleic, or fatty acids;AAA′’, etc., are triglycerides). The re‐esterification is accom‐panied by formation of palmitate‐enriched digly‐ceride —rac‐glyceryl‐1‐palmitate‐2‐oleate(PO‐ OH@@) exceedsrac‐glyceryl‐1,2‐dioleate (OO‐OH) — and glyceryl‐2‐monoleate (HO‐O‐OH). Buffer pH optimum for maximumPOO conversion and palmitate enrich‐ment in 15 min is between 6.0 and 6.5 at 38 C. Hexane is used to dissolveP in the oil phase. In‐creasing the amount of dissolvedP by increasing the amount of hexane added increases palmitate enrich‐ment and decreases reaction rate. At 36 C and 6.0 buffer pH (26 volume %POO and 15 volume %P in oil phase), yields after 3 hr werePOP, 22%;PO‐ OH, 27%; HO‐O‐OH, 11%;POO, 27%; glyceryl‐1,2,3‐tri‐oleate(OOO), 3%; andOO‐OH, 10%.

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